(Z)-3-(4-(Dimethylamino)benzylidene)thiochroman-4-one: Synthesis, Crystal Structure and Molecular Modelling Using Density Functional Theory

  • Neudo UrdanetaEmail author
  • Jesús Núñez
  • Gustavo Liendo
  • Carlos Rivas
  • Teresa González
  • Alexander BriceñoEmail author
Original Paper


The title compound C18H17NOS was synthesized by condensation of thiochroman-4-one with 4-dimethylaminobenzaldehyde. The possible existence of the 3-(4-(Dimethylamino)benzylidene)thiochroman-4-one (E)- and (Z)-geometrical isomers was investigated using B3LYP/6-31G**. Crystallographic and vibrational data are compared with the results of Density Functional Theory (DFT) B3LYP/6-31G** level. Bond orders were estimated using the NBO calculation method correlating with changes in the bond length. To explain deviation of an ideal molecular geometry, the concept of non-equivalent hybrid orbitals was invoked. The studies of X-ray diffraction revealed strong intermolecular interactions between dimers of the compound connected to each other through dipole–dipole interactions S–C, N–C y O–C in the absence of hydrogen bonding.

Graphical Abstract

In this report, a study of the structural characterization of (Z)-3-(4-(dimethylamino)benzyliden)thiochroman-4-one is carried out by spectroscopic methods, single-crystal X-ray diffraction and functional density calculations.


(Z)-3-(4-(Dimethylamino)benzylidene)thiochroman-4-one Crystal structure DFT calculations 



We would like to thank the Centro de Investigaciones Tecnológico y Humanístico de la Universidad Politécnica Territorial del Oeste de Sucre “Clodosbaldo Russian”. We thank FONACIT (Grant No. LAB-97000821) for financial support, Consejo de Investigación de la Universidad de Oriente (Project No. CI 02-010201-1898-14), Proyecto Estratégico Misión Ciencia FONACIT (Grant No. 2007001522). We want to thank the researcher Marielsys Moya for contacting the crystallographers.


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Authors and Affiliations

  1. 1.Departamento de QuímicaUniversidad Simón Bolívar (USB)CaracasVenezuela
  2. 2.Departamento de BiologíaUniversidad Politécnica Territorial del Oeste de Sucre “Clodosbaldo Russian”CumanáVenezuela
  3. 3.Departamento de QuímicaNúcleo de Sucre, Universidad de OrienteCumanáVenezuela
  4. 4.Departamento de CienciasNúcleo de Monagas, Universidad de OrienteMaturínVenezuela
  5. 5.Centro de QuímicaInstituto Venezolano de Investigaciones Científicas (IVIC)CaracasVenezuela

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